Luxury rentals in San Gimignano

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Top-rated luxury vacation rentals in San Gimignano

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Luxe

Villa in Radda in Chianti

5 out of 5 average rating, 9 reviews

Villa Montemaggio

The Tuscan sun soaks into the stone walls of this 17th-century farmhouse—and into the grapes clustered in the organic vineyards in the surrounding Chianti countryside. The Roman road from Siena to Florence once traced these hills; today, they’re home to the 70-hectare Montemaggio estate, which produces organic wine and olive oil. Siena is 40 minutes away by modern road; Florence, 1 hour. Smell the flowers in the gardens, pick fresh mulberries and figs to snack on, and see if you and the kids can find the playhouse hidden away on the estate’s grounds. There’s a private gym for workouts, a swimming pool for refreshment, and a rooftop terrace just made for the evening’s first bottle of local wine. While the villa still has some of its 17th-century farmhouse charm—spot beamed ceilings, doorways framed in elaborate molding, and a wide hearth on the living room fireplace—it’s been fully renovated. A pair of plump sofas invites you to stay a while in the living room, and there are plenty of chairs around the dining table that takes center stage in the fully equipped kitchen. Learn more about the Montemaggio estate by booking a cooking class, featuring fresh produce from the gardens, or a wine tour. Be sure to ask about the festivals in nearby villages, which range from celebrations of wine to a fete dedicated to bruschetta. Beyond Tuscany’s medieval towns and fortresses, the cities of Siena and Florence are close enough for a day trip. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Television, Desk • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Television, Desk FEATURES & AMENITIES • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

Villa in Chiusdino

Quercia

Step outside each morning to feel the warm, fresh breeze as you stroll through fruit gardens and forests of oak at this traditional farmhouse estate in the heart of Tuscany. Embark on day trips to nearby villages, vineyards, and the famous Abbey of San Galgano. Return home for an afternoon swim, a delicious alfresco dinner, and a night of incredible Italian wine by the fireplace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Balcony • Bedroom 3: 2 Twin size beds (can be converted to a king), Day bed, Ensuite bathroom with stand-alone rain & steam shower, Bidet House 2 • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Walk-in closet, Sofa, Desk • Bedroom 5: King size bed, Shared access to hallway bathroom, shower/bathtub combo, Dual vanity, Bidet, Desk • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain & steam shower, Bidet, Walk-in closet, Desk • Bedroom 7: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet OUTDOOR FEATURES • Outdoor living space STAFF & SERVICES Included: • Linen change - twice per week • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Additional housekeeping

Luxe

Place to stay in San Gimignano

4.67 out of 5 average rating, 3 reviews

Villa Simone

Villa Simone, a 15th-century stone villa near San Gimignano, has been beautifully restored, offering rustic Tuscan charm and 6 bedrooms for up to 12 guests. Surrounded by vineyards and olive groves, it features a spacious garden, a pool with Chianti hill views, and a tennis court. This estate produces exceptional olive oil and wines, including Vernaccia di San Gimignano, making it perfect for relaxation and exploring nearby medieval villages and iconic cities like Florence, Siena, and Pisa.

Luxe

Villa in Casole d'Elsa

5 out of 5 average rating, 3 reviews

Villa Sublimis by Villas in Med

This is not just any former stone farmhouse, it’s a unique and elegant villa, that stands as a testament to timeless charm fused with modern luxury. Originally built in the 19th century, this magnificent holiday destination has been expertly transformed to preserve its historical allure while offering an array of contemporary comforts. Nestled amidst the rolling, green Tuscan hills west of Siena, it serves as a serene oasis, perfect for those seeking a one-of-a-kind vacation experience.

Luxe

Villa in Tavarnelle Val di Pesa

4.85 out of 5 average rating, 13 reviews

Villa Chianti Fornace

Experience the epitome of Tuscan luxury at Villa Chianti Fornace — a meticulously restored historic villa nestled between Florence and Siena. This exquisite retreat features expansive gardens, a private spa, and a panoramic pool with sweeping views of rolling vineyards. Whether you're planning a romantic escape or a family holiday, immerse yourself in the authentic charm and serene beauty of the Chianti countryside at this unparalleled haven.

Luxe

Apartment in Centro Storico

Piazza di Santa Croce il Magnifico

Benvenuti a palazzo Barberini, già descritto nel 1531, in un'esclusiva dimora nel cuore di Firenze, situata in uno dei luoghi più iconici della città; Piazza di Santa Croce. Questo splendido appartamento, con una superficie di oltre 300 m² combina l'eleganza dell'architettura rinascimentale con il design italiano contemporaneo, offrendo un soggiorno indimenticabile. Fu studio del grande pittore italiano Pietro Annigoni dal 1933 al 1952.

Luxe

Place to stay in Centro Storico

5 out of 5 average rating, 5 reviews

Luxury Apartment 22

Overlooking Duomo, Via del Corso, and Via dello Studio, this classic Florence apartment is a luxurious home base for your next exciting vacation. From the heart of Florence, you’ll have no trouble getting around to all of the city’s world-famous sites, many by foot. The apartment is decorated with custom furnishings, underfloor heating, and fine Florentine finishes. Copyright © Luxury Retreats. All rights reserved.

Luxe

Villa in Volterra

5 out of 5 average rating, 8 reviews

Villa Finesterra

Preserving the historical character of the structure through an innovative approach: the design of Villa Volterra has been curated with the intention of creating the right balance between rustic and modern, tradition and design. The beating heart of the property is the living area, which is adorned by a panoramic glass wall with a spectacular view of the swimming pool that creates a seamless bridge to the garden.

Luxe

Villa in San Gimignano

5 out of 5 average rating, 4 reviews

Villa Sarah Tenuta Melograni

Villa Sarah enjoys spectacular views of the famous towers of San Gimignano. A large garden surrounds the entire structure and also the four-sided infinity pool with spa whirlpool, made with valuable stone of Cardoso, renowned local stone. Next to the swimming pool is a big dependance with large panoramic terrace, equipped outdoor kitchen, bbq, bar area, relaxation area and a large table to enjoy outdoor dining.

Luxe

Villa in Montecatini Val di Cecina

5 out of 5 average rating, 3 reviews

La Berretta

Experience both traditional and modern Tuscany at La Berretta. Set on a hilltop just outside Pisa, the restored eight-bedroom villa combines rustic architecture with contemporary interiors, and offers 360-degree views of the surrounding hills, too. With accommodations divided between the main house and a three-bedroom guest cottage, La Berretta is ideal for extended families or large groups of friends.